(R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one

Base Information

• Chemical Name: (R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one
• CAS No.: 202745-00-4
• Molecular Formula: C₁₄H₂₁NO₄Si
• Molecular Weight: 295.411
• Mol file: 202745-00-4.mol

Synonyms:

Chemical Property of (R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one

There total 1 articles about (R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-Ethyl-8-methoxy-6-trimethylsilanyl-1H-pyrano[3,4-c]pyridine (174092-77-4) → (R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one (202745-00-4) + (S)-(+)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one (174092-78-5)

Guidance literature:

With osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; iodine; potassium carbonate; calcium carbonate; potassium hexacyanoferrate(III); Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) aq. t-BuOH, 0 deg C, 12 h, 2.) aq. MeOH, r.t., 32 h;

DOI:10.1002/(SICI)1521-3765(199801)4:1<67::AID-CHEM67>3.0.CO;2-F

Reference yield:

(R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one (202745-00-4) → (S)-(+)-20-fluorocamptothecin (828934-85-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 1 h / -78 °C

2.1: 28 percent / ICl / CH₂Cl₂ / 1 h / 20 °C

3.1: sodium iodide; chlorotrimethylsilane / acetonitrile / 0.25 h / 20 °C

3.2: 71 percent / H₂O / acetonitrile / 14 h / 60 °C

4.1: NaH / 1,2-dimethoxy-ethane; dimethylformamide / 0.17 h / 0 °C

4.2: 73 percent / LiBr / 1,2-dimethoxy-ethane; dimethylformamide; toluene / 5 h / 65 °C

5.1: 53 percent / hexamethylditin / benzene / 5 h / 20 °C / Irradiation

With chloro-trimethyl-silane; diethylamino-sulfur trifluoride; hexamethyldistannane; Iodine monochloride; sodium hydride; sodium iodide; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/j.bmcl.2005.07.074

upstream raw materials:

4-Ethyl-8-methoxy-6-trimethylsilanyl-1H-pyrano[3,4-c]pyridine

Downstream raw materials:

(S)-(+)-20-fluorocamptothecin